Clueless Fashion to Inspire Your Wardrobe in 2021

Some days we try to put together the perfect, Instagram-worthy outfit only to realize that it isn’t quite as good as we thought it would be. We sort through different combinations of bottoms and tops, experiment with different styles and add accessories, but still struggle to get that “it girl” look. It isn’t long before we realize that we’re utterly clueless!

But maybe that’s the answer to our fashion dilemma- Clueless! If you’re in need of outfit inspiration, look no further than your favorite streaming service. Many memorable, funny and heartfelt teen movies premiered in the 90s, but few achieved the enduring popularity of Clueless. Clueless follows the story of Beverly Hills teen Cher Horowitz as she rocks fabulous outfits, spouts catchy quotes (“As if!”) and ultimately learns a thing or two about caring for others and accepting that she doesn’t know it all.

Some 90s trends were downright awful- ahem, jeans under dresses and skirts- but Clueless fashion has stood the test of time. Although it premiered in 1995, Clueless remains a prime source of fashion inspiration today and has made a huge impact on how we remember 90s fashion as a whole. Clueless costume designer Mona May is regarded by some as the “Queen of 90s Movie Fashion.” In addition to Clueless, she worked on The Wedding Singer, Never Been Kissed and Romy and Michelle’s High School Reunion, among many other movies. With Clueless, Mona May wanted to steer away from the grunge trend of the early 90s.

“We really tried to bring girliness to this film,” she said in an interview. In turn, Cher’s outfits throughout the film are feminine, preppy and classy. May chose to incorporate several trends from the 60s when crafting Cher’s wardrobe, such as Mary Janes, miniskirts, berets and tweed.

Cher’s outfits are nothing short of iconic. (Of course, all of us would be fashion icons if we had a giant closet equipped with a computer that can generate outfit combinations.) Just like Cher gave new girl Tai a fabulous makeover, you can rely on her to make your next #OOTD amazing. Check out these outfits we’ve put together based on Cher’s best looks that bring Clueless fashion into 2021.

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Cher’s Best Looks (And How to Steal Them!)

Cher’s Back to School Look

Paramount Pictures

The Dolce & Gabbana yellow plaid skirt suit is perhaps the most recognizable outfit of Cher’s, making it a popular Halloween costume. To appear less costume-y, as opposed to an identical yellow plaid look, try this Lovers + Friends short suit. Pair with knee socks and Mary Janes, some of the most important staples in Clueless fashion, to play up Cher’s school girl vibe!

Get the Look:

clueless fashion

HUE Women’s Soft Opaque Knee Socks
Miu Miu Patent Leather Square-Toe Mary Jane Pumps
Lovers + Friends Analee Jacket
Lovers + Friends Analee Short

Driver’s Test Chic

clueless fashion
Paramount Pictures

Even while taking (and failing) her driver’s test, Cher made sure she looked good. Her long, sheer white top looked perfect layered underneath her cropped sweater vest. (And as we know, sweater vests have been taking over since fall 2020.) The sheer white top from Sugar Thrillz was actually designed with Cher in mind!

Get the Look:

clueless fashion


Aritzia Sunday Best Sparrow Vest
Sugar Thrillz I Totally Paused Sheer Top
Motel Rocks Sheny Mini Skirt
Naturalizer Banks Pump

The Cute Cardigan

clueless fashion
Paramount Pictures

Cardigans are on trend for 2021, and Cher got it right when Clueless premiered 26 years ago. Not only did she nail the style, but also the color- light green is currently one of the most popular colors in fashion and home design. Sneakers with bow detailing are a great way to have comfort and functionality while retaining stylishness and femininity.

Get the Look:

clueless fashion

Princess Polly Carrie Mini Skirt
Aritzia Wilfred Sicily Cardigan
Aritzia Sunday Best Cary Tank
NeroGiardini Bow Platform Sneakers

Tanks Over Tees

Paramount PIctures

Proven by her driver’s test look, Cher is an expert at layering. Tank tops and t-shirts are an unlikely but adorable combination, and the matching low heel and pearl earrings pull everything together. This outfit is cute, classy and 90s- everything that constitutes Clueless fashion.

Get the Look:

clueless fashion


Brandy Melville Sheena Bow Tank
Express Fitted Double Layer Crew Neck Tee
Topshop Raw Hem Crop Straight Leg Jeans
Linea Paolo Bardot Pump
Tiffany Ziegfeld Collection Pearl Earrings

Cher’s Date Night Fit

Paramount Pictures

The little red dress will never go out of style. An elegant hair clip, like Cher wore with her little red dress, can elevate the simple look and make it more interesting. It’ll also keep your hair out of your face so your date can see those beautiful features!

Get the Look:


Urban Outfitters Mallory Cowl Neck Slip Dress
Ettika Crystal Striped Brushed Gold Hair Clip
Jimmy Choo Romy Suede Pumps

The Edgy Look

Paramount Pictures

When she attempted to flirt with Josh, Cher looked edgy with a hint of elegance. The sheer top is a necessity for anyone who aims to evoke the 90s with their wardrobe, as is Vivienne Westwood jewelry, which is having a major reprisal.

Get the Look:

Missguided Black Mesh Button Through Shirt
Everlane The Pima Micro-Rib Tank
Mango Pleat Detail Pants
Vivienne Westwood Sorada Bas Relief Pendant
Urban Outfitters Daria Treaded Mary Jane

The Perfect Accessory

Paramount Pictures

What’s the perfect accessory to compliment a preppy outfit and keep it youthful? A headband! Cher’s matching sweater and headband make for an adorable look, and the patterned pants add an element of fun.

Get the Look:


Everlane The Soft Cotton Square Crew
Anthropologie Gingham Picnic Pants
Banana Republic Factory Tailored Non-Iron Shirt
France Luxe Italian Bandeau
Superga 2790 Acotw White

Save the image below to Pinterest so you can come back later!

Madison Deane is an enthusiastic writer based in North Carolina with a passion for fashion, beauty and wholesome living.

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